Synthesis of targetable cationic amphiphiles

Article abstract of DOI:10.1016/S0040-4039(99)01558-0

Cationic amphiphiles 1a-1c, with monosaccharide at the ω-position of the hydrocarbon tails, were synthesized by utilization of Schmidt's trichloroacetimidate procedure for the glycosylation step and application of the commercially available 3,5-dihydroxybenzyl alcohol as a scaffold for the attachment of double hydrocarbon tails. Application of the Zemplen condition for O-deacetylation in the presence of base-sensitive benzyl bromide was found to be efficient. The synthetic route provides an entry for the synthesis of versatile quaternary ammonium amphiphiles having the cell targeting glycosyl ligands.